


experimentation

by vogelwrites



Category: Rusty Quill Gaming (Podcast)
Genre: Alternate Universe, Cunnilingus, F/M, First Time, It's from Wilde's perspective, POV Second Person, Platonic Cuddling, Platonic Relationships, Platonic Sex, Riding, Trust, Vaginal Fingering, Vaginal Sex, You Are Wilde
Language: English
Status: Completed
Published: 2020-06-17
Updated: 2020-06-17
Packaged: 2021-03-04 04:20:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,361
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24767602
Author URL: https://archiveofourown.org/users/vogelwrites/pseuds/vogelwrites
Summary: Sasha's interested in learning something new, and you're more than happy to oblige.
Relationships: Sasha Racket & Oscar Wilde, Sasha Racket/Oscar Wilde
Comments: 6
Kudos: 34
Collections: "Working on the Name" Bar and Brothel





	experimentation

**Author's Note:**

  * For [ExLibrisCraux](https://archiveofourown.org/users/ExLibrisCraux/gifts).



> happy (late, _sorry_ ) birthday to craux! she helped me a lot with battling writing anxieties while i worked on this bad boy, and it feels appropriate that it be her birthday gift. 
> 
> this is written for a very specific au from the wilde ride discord and it's not going to make much sense to anyone else but you're welcome to read anyway (as long as you're 18+, minors fuck off)! a few key points:
> 
> this is an au set in the same location/era as the podcast. it's a brothel type au in which wilde is one of the most profitable prostitutes and sasha is one of his bodyguards. the two have become close over the years and due to past abuse sasha wanted to have positive sexual experiences, and wilde wanted more than anything to prove to her that it doesn't have to hurt or be a negative experience. someone else has written an unposted work where wilde gives her oral for the first time, so i decided to see what it would be like if she asked him to have sex with her to show her. and here we are.
> 
> i know this won't be a lot of people's _thing_ and that's okay! hit the back button if you'd like, i really don't mind. if you've made it this far and still want to read, please do, and let me know what you think!

“Hey, Wilde?” Sasha says, a hand combing through your hair as your head on her chest rises and falls with each of her breaths. You give a quiet mumble of recognition, unwilling to move quite yet. It’s safe here, with Sasha. The trust between you two is safe and comforting, allowing you to forget about the rest of your life for a while. “I-I like this whole… _thing_ we’ve got here but, um, if you’d be interested- maybe we could- I didn’t know if you’d want to, uh, show me some… other things?”

You lift your head up a bit at that. “Other things?” you ask, though you’re fairly certain you know what she means. 

“Yeah. Y’know. The types of stuff people come t’ you for, the stuff people always seem so obsessed with. The, uh,” she coughs and turns away, trying to hide the flush coating her cheeks. “The _rod ‘n the hole_ stuff. Y’know.”

Your face breaks into a small smile, and you can’t help the chuckle that falls through your now-parted lips. _The rod in the hole_. It’s such an unmistakably _Sasha_ thing to say and it makes your heart swell with affection for her. “If that’s what you want, I’m more than happy to show you the ropes, as it were,” you say as you lift yourself off of her chest and roll onto your side. After a moment, you reach out and take one of her hands. “I’ve already said you don’t owe me anything, so if that’s what this is about-”

Her head snaps towards you, a quiet anger blooming behind her eyes. “-‘s not.” 

“Okay, okay,” You whisper, holding a hand up in deference. “When were you thinking about doing this, then?”

She shrugs and looks around the room. "Now's fine."

You freeze. _Now?_ She’s right, now is technically fine for this, you don’t have any more clients tonight and you’re the only person she guards anymore. You scan her face, searching for any sign that she doesn’t actually want this. You find none, so you smile at her before you pull yourself up to sit cross-legged next to her. “Are you sure?” you ask. “We can wait, you know, I’m not going to take it back. It doesn’t _have_ to be now. I won’t go back on my word.”

She sits up as well and turns to face you, scarred face soft and earnest. "I know you won't. I just… think I'm ready now. You're the one who told me it doesn't have to be some big important thing if I don't want it t’be. And I don't. I want it to be nice, y’know, and with someone I… trust."

Something inside you warms when you hear that word. Trust. _Of course she trusts me_ , you think. If she didn’t you wouldn’t be doing what you’ve been doing. She wouldn’t do the job she does. She would have left this job to Grizzop alone ages ago and likely never have talked to you again, if she didn’t trust you. But this feels… different. There’s a deeper meaning to the word this time.

“Okay, then,” you say. “Lay back down for me.” You place a hand on her shoulder and guide her back down onto the mattress. “I need to make sure you’re ready for this, alright? Say the word and I’ll stop.”

You carefully situate yourself between her legs. It’s familiar, comforting, the feeling of being boxed in with only one thing to do. You think back on the first time you’d ever done this with her, how tense and afraid she was, how tense and afraid _you_ were. Every noise she made terrified you, you’d pull back and whisper “alright, Sasha?” into her thigh, and every time she’d whisper back “alright,” and you’d continue. You know you have to be gentle with her, careful not to startle her, but you also know how tough she is. Her strength and resolve impress you at every turn, with each new scar you discover you find yourself caring for her more and more.

You _have_ to make this good for her. This can not be another traumatizing first in her life, another thing for her to use as a reason to push everyone away, to push _you_ away. Gently, you place one hand on the outside of her thigh and lean your head in towards her sex. This is normal, this is routine. You let out a soft breath directly onto her, to warn her not to startle as you lick a stripe up to her clit. Sasha’s always quiet when you do this. Doesn’t always come, either, sometimes she just likes to enjoy it without focusing on an end goal. If it were anyone else you’d be worried, possibly even _offended_ , but it’s Sasha, and you know soft gasps and huffs of breath are the highest form of praise you’ll ever receive. 

Focusing on the movements of your tongue, Sasha doesn’t even notice you raising a hand up to her sex until you’re brushing your fingers along the crease of her thigh. She jolts, a movement so minuscule anyone but you wouldn’t have come close to noticing. But you’re so in tune with her, so used to monitoring every seemingly insignificant noise or twitch she makes and you instantly freeze.

“All right, Sasha?”

“Y-yeah,” her voice shakes. “I- I know you have t’ go _inside_. I know that. Jus’- slow, yeah?”

You nod. “Of course.” You don’t say that you were going to go slow anyway, don’t mention to her that you understand the stakes here or how fragile she looks like this. It won’t end well. “All right to continue?” You ask, moving a finger to tease across her core, savoring the way her thighs shake around your head. She gives a soft, barely-there affirmation and you press your first finger inside of her so slowly you hardly feel you’re moving at all. It takes what feels like years for your finger to be fully seated in her, giving her clit soft kitten licks as a distraction while she wiggles and grunts and gets used to the stretch and sensation.

“Huh.” 

You freeze, looking up at her with trepidation, finger still knuckle deep in the warm, wet heat of her. Almost dazed, she looks down at you and, after a long, heart-stopping second, nods. “G’ on then, Wilde.” 

A smile inches its way onto your face as you work her open. You only add a second finger once you’re unwaveringly positive she’s ready. She’s different like this, when you’re locked between her thighs, making her whine and whimper and roll her hips with your fingers, chasing them as you pull them out only to cry out as you push them back in. She feels… fragile. Easily spooked, easily broken. The simplest mistake, one wrong decision could send her into a kind of spiral you’ve only seen from her twice in the entire time you’ve known her. It puts you on edge as you pleasure her, but that is decidedly not a negative for you as you feel the hair on your neck standing up, your cock straining against the mattress.

You place a kiss to the meat of her inner thigh, fingers continuing their ministrations, opening her up with deliberate movements, and she sighs so softly you nearly miss it. “Tell me when you’re ready. Take as long as you need, I’m more than happy to do this forever,” you tell her, and you mean every word. She knows you do, but she still meets your eyes, fierce resolve and determination behind them.

“Ready.”

“Are you sure?”

Her eyes narrow, annoyance beginning to show in her features.

“Sorry. I just… worry.” She rolls her eyes, but you can feel the affection behind it. “I have an idea of how to go about this, if you’re amenable to it. I’m going to get on my back and you’re going to ride me. That way you hold the power, as it were.”

“Yeah- yeah that sounds. Sounds perfect.” She’s breathless as you slide your fingers out and wipe them quickly on the sheets. As soon as you’re sufficiently clean she scoots over to allow you to take the position she was just in. She watches you as you situate yourself, eyes flipping between your face and your body, chewing on a fingernail in anticipation.

You place yourself on your back, head against a pleasantly soft pillow, prick flushed and standing proudly as Sasha stares at you. You don’t push, don’t make any gestures or facial expressions that would cause her to think you’re forcing her to make a decision. You watch her face intently, you scan and catalog the different expressions she goes through, and the second you recognize resolve in it she moves. She flings a leg across you to straddle your waist and nearly tumbles as she works out the best angle to hold her legs at as the mattress dips and shifts around you.

She meets your eyes, hers wide and nervous but fiercely determined, places one hand on your chest to keep herself steady as she uses the other the gingerly line herself up to your long-neglected prick. You stay as still as you can as she sinks down onto you. Slowly, _so slowly._ It takes all your strength not to buck up into the wet heat surrounding you. Looking at her face, you see her eyes shut tightly, mouth open in a small “o” as she continues to lower herself onto your cock. You can tell she’s straining, wanting to take more without hurting herself. You reach out with a hand, searching the space for one of hers to hold while she continues her descent. The instant your hand wraps around hers you watch her features soften _just_ so as she relaxes with your touch. 

Minutes pass, though they feel like hours as she continues, warmth enveloping more and more of you until she’s fully seated against your hips. You’re shaking now, each minuscule movement of her body has you forcing down whines as they send the most delicious sensations up your spine. You shove your free hand against your mouth, biting down to muffle the sounds bubbling up through your chest. Sasha looks at you and you see the corner of her mouth twitch up.

“All right, Wilde?” She asks, a smirk playing at her lips, eyes as she carefully lifts herself back up before sinking down again. Her thighs shake, due to physical exertion or nerves you’re not sure, but she’s unsurprisingly adept at keeping herself upright as she ups her speed. You can’t help the smile that forces its way onto your face as you watch her relax, watch her expression change from one of worry and almost-but-not-quite fear to one of understanding. “Ha- I. I get it now,” she gasps out as she drops down harder than she has so far. Her movements still for a moment as she thinks, and then you hear a questioning sound before she rolls her hips in a small circle. It’s a short circle, exploratory in its motion, but it knocks the breath out of you all the same.

“ _Fuck_ ,” you groan, dropping your hand from your mouth and grabbing at the sheets with it. You look up at her and she does it again. She seems to delight in the reactions she pulls from you, picking up her pace and varying her movements to elicit more of them. “Sasha- I,” you clear your throat. “I won’t last if you keep that up.”

Sasha nods and slows, but doesn’t stop. “Y’ take your meds?” she asks.

“Every day.” 

Instead of replying, she just stares at you and drops down _hard_ onto your cock, smiling at your resulting moan. _How is she so good at this?_ you think. You know she’s a smart girl, but you never expected her to pick this up so quickly, to be so skilled it would reduce a lesser man than you to mindless begs and whimpers. 

She gives a very pointed thrust downwards that shuts your inner monologue completely off, and you can feel your orgasm building rapidly. “Sasha-” you warn. She just gives you a pointed look, another _perfectly_ angled roll, and you’re gone. Your hands fly up and grab her waist, holding her against you as you still and groan. 

When you finally recover, she gives you a smirk and climbs gently off of you. Standing next to the bed, she crosses her arms over her chest and looks you over. She’s shaking, almost imperceptibly, minuscule trembles in her fingers giving her away. You reach out and cover your hands with hers. “Good?” you ask, running your thumb along the back of one of her hands as she comes back to herself. “Did you want to come?”

She shakes her head. “Not. Not this time, yeah? Tha’- that was… interestin’. New. Not bad! Just… I’m a little…” Sasha trails off, squeezing your hand tight.

“I understand. I do have to say, you picked it up _very_ quickly. I wasn’t expecting to finish so soon,” you laugh, and the sound of it makes her smile, a sliver of tension easing from her shoulders. You know you won’t ease all of her anxieties, but the little bit you _can_ do makes your heart swell with love for her, a special kind of love that only Sasha can evoke in you.

She tilts her head to the side, confused. "Wot d’you mean? I don't jus' stare at the door when I guard, y'know? You can’t watch this kinda stuff without learnin’ at least a few things. I know ya gotta, like, wiggle.... 'n stuff."

"... and stuff." You shake your head at her, a smile wide across your face, and quickly tug on the clothing you’d left in a pile near the bed ages ago. She does the same, snatching a dagger out of her jacket pocket and holding it close as she heads for the door.

“See ya tomorrow, yeah?” She calls as she walks through the doorway.

You let out a deep sigh. “Yeah. Tomorrow.”

**Author's Note:**

> thanks to the ride once again and forever. couldn't do it without you lot.


End file.
